Abstract
Both a three-step and a five-step syntheses of monoterpene alkaloid (±)-oxerine from alcohol 6 have been accomplished. In the second approach, the synthetic efficiency was enhanced by implementing a one-pot protocol (deprotonation/silylation/ alkylation/desilylation). The construction of the cyclopenta[ c]pyridine framework was realized by an intramolecular Heck reaction, which should be adaptable for the synthesis of other related monoterpene pyridine alkaloids.
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